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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:35:03 UTC

Update Date

2022-03-07 02:52:26 UTC

HMDB ID

HMDB0030145

Secondary Accession Numbers

HMDB30145

Metabolite Identification

Common Name

Ascochitine

Description

Ascochitine belongs to the class of organic compounds known as salicylic acid and derivatives. Salicylic acid and derivatives are compounds containing a 2-hydroxybenzoic acid moiety or a derivative thereof. Based on a literature review a significant number of articles have been published on Ascochitine.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0030145
     RDKit          3D
Ascochitine
 36 37  0  0  0  0  0  0  0  0999 V2000
   -4.6797    1.0689    0.8582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2330    0.7393    1.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5061    0.5335   -0.2727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1316   -0.6043   -1.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718    0.2795    0.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6750    0.2013    1.3208 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5475   -0.0163    1.7109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5450   -0.1856    0.7751 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8612   -0.4193    1.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3021   -0.5055    2.3863 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8250   -0.5822    0.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2202   -0.8298    0.4144 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6301   -0.9095    1.5878 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1282   -0.9828   -0.6102 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3894   -0.4970   -1.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2755   -0.6469   -2.1202 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0922   -0.2662   -1.5970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1356   -0.1044   -0.6199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1940    0.1321   -0.9936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5812    0.2121   -2.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0262    1.9130    1.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2639    0.1336    1.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8328    1.2711   -0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0755   -0.1962    1.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6671    1.5288    1.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5560    1.4401   -0.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7194   -0.2394   -1.9169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3767   -1.3115   -1.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8726   -1.1555   -0.4095 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8178   -0.0708    2.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6968   -0.4045    3.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3471   -0.1322   -1.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7663   -0.2023   -2.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6185   -0.7772   -2.9208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0869    0.9181   -2.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5860    0.6679   -2.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19  5  2  0
 18  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  4 29  1  0
  7 30  1  0
 10 31  1  0
 14 32  1  0
 17 33  1  0
 20 34  1  0
 20 35  1  0
 20 36  1  0
M  END

  Mrv0541 02241219272D          

 20 21  0  0  0  0            999 V2000
    2.8870    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8870   -0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1446   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4021   -0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4021    0.4121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6596    0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0004    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421    0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4846    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4846   -0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0004   -0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6596   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6596   -1.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8870    0.4121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1446    0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2271    1.6496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1446   -1.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1446   -0.8246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421    1.6496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 18  1  0  0  0  0
  4  5  1  0  0  0  0
  4 13  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  2  0  0  0  0
  8 20  1  0  0  0  0
  9 10  1  0  0  0  0
  9 16  1  0  0  0  0
 10 11  1  0  0  0  0
 10 19  2  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030145

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(C)C1=C(C)C2=CC(=O)C(C(O)=O)=C(O)C2=CO1

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O5/c1-4-7(2)14-8(3)9-5-11(16)12(15(18)19)13(17)10(9)6-20-14/h5-7,17H,4H2,1-3H3,(H,18,19)

> <INCHI_KEY>
DZBCEUTUWOWUDY-UHFFFAOYSA-N

> <FORMULA>
C15H16O5

> <MOLECULAR_WEIGHT>
276.2845

> <EXACT_MASS>
276.099773622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
28.2870894711904

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(butan-2-yl)-8-hydroxy-4-methyl-6-oxo-6H-isochromene-7-carboxylic acid

> <ALOGPS_LOGP>
2.52

> <JCHEM_LOGP>
1.7451976053333338

> <ALOGPS_LOGS>
-3.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.381653514299737

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7941786826768773

> <JCHEM_PKA_STRONGEST_BASIC>
4.184366929542328

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
75.79679999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.28e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-hydroxy-4-methyl-6-oxo-3-(sec-butyl)isochromene-7-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030145
     RDKit          3D
Ascochitine
 36 37  0  0  0  0  0  0  0  0999 V2000
   -4.6797    1.0689    0.8582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2330    0.7393    1.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5061    0.5335   -0.2727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1316   -0.6043   -1.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718    0.2795    0.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6750    0.2013    1.3208 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5475   -0.0163    1.7109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5450   -0.1856    0.7751 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8612   -0.4193    1.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3021   -0.5055    2.3863 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8250   -0.5822    0.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2202   -0.8298    0.4144 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6301   -0.9095    1.5878 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1282   -0.9828   -0.6102 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3894   -0.4970   -1.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2755   -0.6469   -2.1202 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0922   -0.2662   -1.5970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1356   -0.1044   -0.6199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1940    0.1321   -0.9936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5812    0.2121   -2.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0262    1.9130    1.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2639    0.1336    1.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8328    1.2711   -0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0755   -0.1962    1.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6671    1.5288    1.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5560    1.4401   -0.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7194   -0.2394   -1.9169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3767   -1.3115   -1.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8726   -1.1555   -0.4095 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8178   -0.0708    2.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6968   -0.4045    3.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3471   -0.1322   -1.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7663   -0.2023   -2.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6185   -0.7772   -2.9208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0869    0.9181   -2.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5860    0.6679   -2.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19  5  2  0
 18  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  4 29  1  0
  7 30  1  0
 10 31  1  0
 14 32  1  0
 17 33  1  0
 20 34  1  0
 20 35  1  0
 20 36  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       5.389   0.769   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.389  -0.769   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.003  -1.539   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.617  -0.769   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.617   0.769   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.231   1.539   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.001   0.769   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.385   1.539   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.771   0.769   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.771  -0.769   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.385  -1.539   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.001  -0.769   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.231  -1.539   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.231  -3.079   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -5.389   0.769   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -4.003   1.539   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.157   3.079   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.003  -3.079   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.003  -1.539   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.385   3.079   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12    7   11   13                                                  
CONECT   13    4   12   14                                                  
CONECT   14   13                                                            
CONECT   15   16                                                            
CONECT   16    9   15   17                                                  
CONECT   17   16                                                            
CONECT   18    3                                                            
CONECT   19   10                                                            
CONECT   20    8                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0030145
HETATM    1  C1  UNL     1      -4.680   1.069   0.858  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.233   0.739   1.054  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.506   0.534  -0.273  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.132  -0.604  -1.052  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.072   0.279   0.060  1.00  0.00           C  
HETATM    6  O1  UNL     1      -0.675   0.201   1.321  1.00  0.00           O  
HETATM    7  C6  UNL     1       0.548  -0.016   1.711  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.545  -0.186   0.775  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.861  -0.419   1.090  1.00  0.00           C  
HETATM   10  O2  UNL     1       3.302  -0.506   2.386  1.00  0.00           O  
HETATM   11  C9  UNL     1       3.825  -0.582   0.087  1.00  0.00           C  
HETATM   12  C10 UNL     1       5.220  -0.830   0.414  1.00  0.00           C  
HETATM   13  O3  UNL     1       5.630  -0.910   1.588  1.00  0.00           O  
HETATM   14  O4  UNL     1       6.128  -0.983  -0.610  1.00  0.00           O  
HETATM   15  C11 UNL     1       3.389  -0.497  -1.218  1.00  0.00           C  
HETATM   16  O5  UNL     1       4.276  -0.647  -2.120  1.00  0.00           O  
HETATM   17  C12 UNL     1       2.092  -0.266  -1.597  1.00  0.00           C  
HETATM   18  C13 UNL     1       1.136  -0.104  -0.620  1.00  0.00           C  
HETATM   19  C14 UNL     1      -0.194   0.132  -0.994  1.00  0.00           C  
HETATM   20  C15 UNL     1      -0.581   0.212  -2.424  1.00  0.00           C  
HETATM   21  H1  UNL     1      -5.026   1.913   1.486  1.00  0.00           H  
HETATM   22  H2  UNL     1      -5.264   0.134   1.081  1.00  0.00           H  
HETATM   23  H3  UNL     1      -4.833   1.271  -0.232  1.00  0.00           H  
HETATM   24  H4  UNL     1      -3.076  -0.196   1.649  1.00  0.00           H  
HETATM   25  H5  UNL     1      -2.667   1.529   1.588  1.00  0.00           H  
HETATM   26  H6  UNL     1      -2.556   1.440  -0.897  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.719  -0.239  -1.917  1.00  0.00           H  
HETATM   28  H8  UNL     1      -2.377  -1.312  -1.392  1.00  0.00           H  
HETATM   29  H9  UNL     1      -3.873  -1.156  -0.410  1.00  0.00           H  
HETATM   30  H10 UNL     1       0.818  -0.071   2.767  1.00  0.00           H  
HETATM   31  H11 UNL     1       2.697  -0.404   3.170  1.00  0.00           H  
HETATM   32  H12 UNL     1       6.347  -0.132  -1.148  1.00  0.00           H  
HETATM   33  H13 UNL     1       1.766  -0.202  -2.627  1.00  0.00           H  
HETATM   34  H14 UNL     1      -0.619  -0.777  -2.921  1.00  0.00           H  
HETATM   35  H15 UNL     1       0.087   0.918  -2.987  1.00  0.00           H  
HETATM   36  H16 UNL     1      -1.586   0.668  -2.489  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4    5   26
CONECT    4   27   28   29
CONECT    5    6   19   19
CONECT    6    7
CONECT    7    8    8   30
CONECT    8    9   18
CONECT    9   10   11   11
CONECT   10   31
CONECT   11   12   15
CONECT   12   13   13   14
CONECT   14   32
CONECT   15   16   16   17
CONECT   17   18   18   33
CONECT   18   19
CONECT   19   20
CONECT   20   34   35   36
END

HMDB0030145
     RDKit          3D
Ascochitine
 36 37  0  0  0  0  0  0  0  0999 V2000
   -4.6797    1.0689    0.8582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2330    0.7393    1.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5061    0.5335   -0.2727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1316   -0.6043   -1.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718    0.2795    0.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6750    0.2013    1.3208 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5475   -0.0163    1.7109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5450   -0.1856    0.7751 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8612   -0.4193    1.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3021   -0.5055    2.3863 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8250   -0.5822    0.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2202   -0.8298    0.4144 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6301   -0.9095    1.5878 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1282   -0.9828   -0.6102 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3894   -0.4970   -1.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2755   -0.6469   -2.1202 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0922   -0.2662   -1.5970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1356   -0.1044   -0.6199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1940    0.1321   -0.9936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5812    0.2121   -2.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0262    1.9130    1.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2639    0.1336    1.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8328    1.2711   -0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0755   -0.1962    1.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6671    1.5288    1.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5560    1.4401   -0.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7194   -0.2394   -1.9169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3767   -1.3115   -1.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8726   -1.1555   -0.4095 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8178   -0.0708    2.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6968   -0.4045    3.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3471   -0.1322   -1.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7663   -0.2023   -2.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6185   -0.7772   -2.9208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0869    0.9181   -2.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5860    0.6679   -2.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19  5  2  0
 18  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  4 29  1  0
  7 30  1  0
 10 31  1  0
 14 32  1  0
 17 33  1  0
 20 34  1  0
 20 35  1  0
 20 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ascochytin	HMDB
3-(Butan-2-yl)-8-hydroxy-4-methyl-6-oxo-6H-isochromene-7-carboxylate	HMDB

Chemical Formula

C₁₅H₁₆O₅

Average Molecular Weight

276.2845

Monoisotopic Molecular Weight

276.099773622

IUPAC Name

3-(butan-2-yl)-8-hydroxy-4-methyl-6-oxo-6H-isochromene-7-carboxylic acid

Traditional Name

8-hydroxy-4-methyl-6-oxo-3-(sec-butyl)isochromene-7-carboxylic acid

CAS Registry Number

3615-05-2

SMILES

CCC(C)C1=C(C)C2=CC(=O)C(C(O)=O)=C(O)C2=CO1

InChI Identifier

InChI=1S/C15H16O5/c1-4-7(2)14-8(3)9-5-11(16)12(15(18)19)13(17)10(9)6-20-14/h5-7,17H,4H2,1-3H3,(H,18,19)

InChI Key

DZBCEUTUWOWUDY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as salicylic acid and derivatives. Salicylic acid and derivatives are compounds containing a 2-hydroxybenzoic acid moiety or a derivative thereof.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Salicylic acid and derivatives

Alternative Parents

Substituents

Benzopyran
Salicylic acid or derivatives
2-benzopyran
1-hydroxy-4-unsubstituted benzenoid
Heteroaromatic compound
Vinylogous acid
Cyclic ketone
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030145)
Cell membrane (HMDB: HMDB0030145)

Source

Endogenous

Endogenous (HMDB: HMDB0030145)

Exogenous

Food

Food (HMDB: HMDB0030145)

Exogenous (HMDB: HMDB0030145)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	196 - 198 °C	Not Available
Boiling Point	495.25 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	914.9 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.231 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.23 g/L	ALOGPS
logP	2.52	ALOGPS
logP	1.75	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	1.79	ChemAxon
pKa (Strongest Basic)	4.18	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	75.8 m³·mol⁻¹	ChemAxon
Polarizability	28.29 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	168.718	30932474
DeepCCS	[M-H]-	166.36	30932474
DeepCCS	[M-2H]-	199.803	30932474
DeepCCS	[M+Na]+	175.552	30932474
AllCCS	[M+H]+	162.7	32859911
AllCCS	[M+H-H2O]+	159.1	32859911
AllCCS	[M+NH4]+	166.1	32859911
AllCCS	[M+Na]+	167.1	32859911
AllCCS	[M-H]-	167.3	32859911
AllCCS	[M+Na-2H]-	167.3	32859911
AllCCS	[M+HCOO]-	167.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ascochitine	CCC(C)C1=C(C)C2=CC(=O)C(C(O)=O)=C(O)C2=CO1	3065.9	Standard polar	33892256
Ascochitine	CCC(C)C1=C(C)C2=CC(=O)C(C(O)=O)=C(O)C2=CO1	2213.7	Standard non polar	33892256
Ascochitine	CCC(C)C1=C(C)C2=CC(=O)C(C(O)=O)=C(O)C2=CO1	2474.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ascochitine,1TMS,isomer #1	CCC(C)C1=C(C)C2=CC(=O)C(C(=O)O[Si](C)(C)C)=C(O)C2=CO1	2410.0	Semi standard non polar	33892256
Ascochitine,1TMS,isomer #2	CCC(C)C1=C(C)C2=CC(=O)C(C(=O)O)=C(O[Si](C)(C)C)C2=CO1	2414.8	Semi standard non polar	33892256
Ascochitine,2TMS,isomer #1	CCC(C)C1=C(C)C2=CC(=O)C(C(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C2=CO1	2426.9	Semi standard non polar	33892256
Ascochitine,1TBDMS,isomer #1	CCC(C)C1=C(C)C2=CC(=O)C(C(=O)O[Si](C)(C)C(C)(C)C)=C(O)C2=CO1	2669.5	Semi standard non polar	33892256
Ascochitine,1TBDMS,isomer #2	CCC(C)C1=C(C)C2=CC(=O)C(C(=O)O)=C(O[Si](C)(C)C(C)(C)C)C2=CO1	2676.7	Semi standard non polar	33892256
Ascochitine,2TBDMS,isomer #1	CCC(C)C1=C(C)C2=CC(=O)C(C(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C2=CO1	2888.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ascochitine GC-MS (Non-derivatized) - 70eV, Positive	splash10-002b-1290000000-edb53b46daad4e0fa87c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ascochitine GC-MS (2 TMS) - 70eV, Positive	splash10-0abc-9418700000-5d3fbe91af5a02ae4c53	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ascochitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ascochitine 10V, Positive-QTOF	splash10-004i-0090000000-e71d7534ec479cefa502	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ascochitine 20V, Positive-QTOF	splash10-0a7i-0090000000-99dc9a91546f1a63a095	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ascochitine 40V, Positive-QTOF	splash10-0a4r-3690000000-2e6c1c552a17639d56b4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ascochitine 10V, Negative-QTOF	splash10-003r-0090000000-51e2653ac55450309aa8	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ascochitine 20V, Negative-QTOF	splash10-001i-0090000000-be042ff2ae3b3466cf48	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ascochitine 40V, Negative-QTOF	splash10-0f8a-2970000000-68cb13d8d83bed55bded	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ascochitine 10V, Negative-QTOF	splash10-0059-0090000000-be814a1e37f123f8122c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ascochitine 20V, Negative-QTOF	splash10-0ke9-0190000000-9eaf3e871ed98e842713	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ascochitine 40V, Negative-QTOF	splash10-0le9-1960000000-ba24420c1d0212e6481b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ascochitine 10V, Positive-QTOF	splash10-0a4i-0090000000-460142e3c6779d2b31a0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ascochitine 20V, Positive-QTOF	splash10-0a4i-0090000000-e433d99607665a5a67c8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ascochitine 40V, Positive-QTOF	splash10-054n-1920000000-9f28bb9455e1c600062d	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001953

KNApSAcK ID

C00052826

Chemspider ID

35013144

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

270972

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1529511

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Ascochitine (HMDB0030145)

MOL for HMDB0030145 (Ascochitine)

3D MOL for HMDB0030145 (Ascochitine)

3D SDF for HMDB0030145 (Ascochitine)

3D-SDF for HMDB0030145 (Ascochitine)

PDB for HMDB0030145 (Ascochitine)

3D PDB for HMDB0030145 (Ascochitine)

SMILES for HMDB0030145 (Ascochitine)

INCHI for HMDB0030145 (Ascochitine)

Structure for HMDB0030145 (Ascochitine)

3D Structure for HMDB0030145 (Ascochitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra